Yep, all of that will fit in the Pilot no problem, with room to spare! And it's a great travel bag. I routinely (like more than 1/2 my trips) travel with just the Pilot as my one-bag, so I know that it fits great under the seat. It's one of the reasons I went with the Pilot, so that I can stand it up under the seat, and still have room for my feet when I'm travelling an airline where I can't get overhead bin space.

All of these items, and then some! Will fit in the pilot. My only concern would be the lunch box. A lunch box like that is great, but if you’ve got a wet lunch then you’d have to put it vertically and risk some leaking out or whatever. I’ve never been comfortable with that prospect. For that reason I’d maybe consider a makers bag. Just saying. Or a yeoman mini if you can deal with clutter of no organisation at all.

Or get a different shaped lunch box (tall and thin instead of short and wide).

Just my thoughts based on my experience with the yeoman and the pilot.

All of these items, and then some! Will fit in the pilot. My only concern would be the lunch box. A lunch box like that is great, but if you’ve got a wet lunch then you’d have to put it vertically and risk some leaking out or whatever. I’ve never been comfortable with that prospect. For that reason I’d maybe consider a makers bag. Just saying. Or a yeoman mini if you can deal with clutter of no organisation at all.

Or get a different shaped lunch box (tall and thin instead of short and wide).

Just my thoughts based on my experience with the yeoman and the pilot.

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At ~4" wide, it should nestle somewhat on the bottom of the main compartment of the Pilot, especially if it can intrude on the front pockets. It wouldn't be perfectly flat on the bottom, but I don't think they'd have to stand it vertically. I agree with you vertically I'd be concerned about it leaking (I've seen others like that leak), but with the lack of a laptop, I don't really see the need.